Stephen Dubner Talks 'Freakonomics' — and How He …

This story appears in the December 2017 issue of Entrepreneur. Subscribe »

Behold the weird entrepreneurial trajectory of Stephen Dubner. He starts out as a working journalist and profiles a brilliant, quirky economist named Steven Levitt for The New York Times Magazine, then ends up co-writing the runaway bestseller Freakonomics with him, followed by sequels that together sell in the ballpark of eight million copies.

He hits the speaker circuit and launches a show called Freakonomics Radio that also blows up. This inspires him to start a podcast production company, Renbud Radio, to launch more fun, fascinating shows, such as Tell Me Something I Don’t Know, a new one in which smart people tell him…well, you saw the title.

Now this former scribe suddenly finds himself running a business and managing people. And as he told us recently, it’s been a bit of an adjustment.

You started out as a journalist, wound up co-writing the Freakonomics books, and now you’re growing a podcasting company. How’d it happen?

The podcast began not by accident but as a lark. It was 2010, and Steven Levitt and I had just finished our second book, SuperFreakonomics. I’d done a lot of radio and TV as the Freakonomics co-writer, but I never really enjoyed being a guest on other people’s shows, because you don’t have a good control of anything. I thought, I like the medium; it might be nice to actually have a show that could be mine. One of my big inspirations was Tavis Smiley. I really liked that he had created this whole ecosystem he controlled, that he built around the possibility of him expressing his ideas. So I hired this really great producer, and we produced a few episodes and released them as Freakonomics Radio. It was just a fun thing, but it grew and grew and became my main thing. 

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You and Steven Levitt are a really high-profile duo, but you don’t always work together. What’s the process for launching a Freakonomics-branded project that he’s not involved in? Does it ever get awkward?

For us, it’s comically simple. Basically, one of us will say to the other, “Hey, I’m thinking about doing this thing. Do you want to do it?” And then it’s either yes or no. And if it’s no, it’s like, “Well, if you don’t want to do it, how do you feel about me doing it?” “Yeah, great. Have fun.” That’s pretty much what this is. Levitt’s done things like written an econ textbook that had a bunch of Freakonomics stuff in it, and he started a consulting firm. In those cases, he asked me if I wanted to be more involved, and the answer was no. But I’m happy to help him do whatever he wants to do to get that going. And the same with me.

What have you learned from being in a successful partnership? 

I think the thing I’ve learned is that you can try to legislate things in partnerships — and I understand that is the way of the world, that you try to spell out every possible iteration and permutation in a contract. But that, in my experience, has A, taken a really long time and B, pre-created a lot of tension and friction. A better model for me has been to just partner with people I think are smart, and honest and decent.

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I feel like preparing for every eventuality requires you to sit down and think, What awful things is this person capable of, and how can I protect myself against the monster he’s likely to become?

[laughs] That is exactly right.

You started your company about a year ago. What’s it been like going from lone writer to corporate honcho?

Running the company is so not my thing. I’m terrible at it. I’m really good at managing myself, but I’m not good at managing other people. They say that for a lot of managers — especially at the CEO level — one problem is that whenever anyone comes to you, it’s with a problem. They’re not coming here to just say, “Hey everything’s going OK. You’re doing a great job. You look really handsome today. We love you.” It’s like the minute someone walks in the door, you know you’re going to deal with a problem. 

And here’s the thing about me. Usually, most of my correspondence with people is when I have a problem. They do all this amazing stuff all the time, and I try to be grateful, but most of my emails are like, “What went wrong here? Why didn’t we do this?” So if nothing else, I’ve reversed the CEO paradigm, and I’ve become the pain in the ass. Fortunately, I hired a great chief of staff, and she takes care of most of the management.

Have you learned a lot from watching how she manages?

I have. First of all, she is nice — which may sound like an obvious thing, but it’s really helpful. I think I’m a fairly nice person, but when it comes to working, the word people use for me is “exacting,” which I think is a way to say…you know. 

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That you’re a pain in the ass. 

Yeah, I’m a pain in the ass. Because here’s the problem: If you’re a writer, you’ll spend 25 seconds thinking about whether or not to use a semicolon here. That can be troublesome when you’re working with 10 people. If you’re like that with every one of those people, on every decision, that does turn you into a major pain in the ass. You have to learn to communicate it in a way that is not punitive.

I’ve toggled back and forth between being a writer and being a manager, and I always think of it as: You can’t be as mean to other people as you are to yourself. 

[laughs] Yeah. And I think you have to be a better actor than I’m able to be when you’re really pissed off. That’s one thing I’ve been working on. I see something that’s not done well, and I’ll try to cool out for an hour and then say, “Hey, I think the next time we do this, a better way might be blah blah blah,” as opposed to “Why on earth did you think this is a good idea?” Because that’s what my initial thought is. 

There are a lot of parallels between that and a lot of entrepreneurs who start businesses. They have 100 percent control over the thing in the beginning, it grows very organically out of their own sensibility, and then, as they grow, they have to accommodate more people, viewpoints and voices.

Oh, yeah, sure. The biggest lesson I’ve learned was from my father-in-law. He did a lot of things back in the relatively early days of global clothing manufacturing that took a lot of gall. He was really good at looking at the way things are done and saying, “You know, I think I’m going to do something different, and it’s probably going to piss people off,” and he would find all kinds of ways to succeed and win. But the problem is, that kind of entrepreneurial feel is often not compatible with the energy you need to run the companies. The energy that goes into having the ideas, and the attitude that goes into putting those ideas through, even when the world is against you, can often be really counter to the energy and strategies you need to manage well and to run things smoothly.

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Well, for what it’s worth, I’d say your entrepreneurial instincts have served you pretty well so far. 

We haven’t talked about all the things I’ve done that failed. [laughs] The other thing is, I’ve learned a lot from Levitt. In addition to being a good friend and a really great partner, he’s a great teacher. He will say a lot of things like, “You should just basically follow what’s fun for you, because it’s hard to have enough energy to do a lot of work on things that aren’t fun.” If you’re in a position to do it, just pick the thing that you can’t wait to get up and do every morning, and you’ll be way ahead of everybody. For me, that’s been a big guiding principle.